Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides

doi:10.6023/cjoc202106044

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4798-4807.DOI: 10.6023/cjoc202106044 Previous Articles Next Articles

Special Issue: 绿色合成化学专辑

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N-羟乙基-N-芳基丙炔酰胺的无金属硒化螺三环化反应

王玉超^a^,^b, 刘晋彪^a^,^*(), 邱观音生^b^,^*(), 杨宇^b, 周宏伟^b^,^*()

a 江西理工大学材料冶金化学学部江西赣州 341000
b 嘉兴学院生物与化学工程学院浙江嘉兴 314001

收稿日期:2021-06-24 修回日期:2021-08-22 发布日期:2021-09-02
通讯作者: 刘晋彪, 邱观音生, 周宏伟
基金资助:
国家自然科学基金(21772067); 国家自然科学基金(21762018); 国家自然科学基金(21961014); 江西省自然科学基金(20192BCBL23009); 江西省自然科学基金(20202BABL203005); 江西省青年井冈学者奖励计划资助项目

Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides

Yuchao Wang^a^,^b, Jinbiao Liu^a(), Guanyinsheng Qiu^b(), Yu Yang^b, Hongwei Zhou^b()

a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000
b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001

Received:2021-06-24 Revised:2021-08-22 Published:2021-09-02
Contact: Jinbiao Liu, Guanyinsheng Qiu, Hongwei Zhou
Supported by:
National Natural Science Foundation of China(21772067); National Natural Science Foundation of China(21762018); National Natural Science Foundation of China(21961014); Natural Science Foundation of Jiangxi Province(20192BCBL23009); Natural Science Foundation of Jiangxi Province(20202BABL203005); Youth Jinggang Scholars Program in Jiangxi Province

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Abstract

Facile ipso-cyclization and regioselective ortho-capture of N-hydroxylethyl-N-arylpropiolamides are reported for the synthesis of various selenium-containing benzo[b]pyrrolo[2,1-c][1,4]oxazin-3-ones. The reaction works well with high efficiency and broad reaction scope. In the process, it is believed that α-addition of the propiolamide, sequential ipso-cyclization of the aniline, and regioselective ortho-capture with a hydroxyl group are involved.

Key words: selenization, dearomatization, ipso-cyclization, N-hydroxylethyl-N-phenylpropiolamide

Cite this article

Yuchao Wang, Jinbiao Liu, Guanyinsheng Qiu, Yu Yang, Hongwei Zhou. Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4798-4807.

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Entry	Oxidant (equiv.)	Solvent	Temp./℃	Yield^a/% of 3a
1	Oxone (2.0)	CH₃CN	80	61
2	Oxone (2.0)	DCE	80	20
3	Oxone (2.0)	THF	80	17
4	Oxone (2.0)	DMSO	80	44
5	Oxone (2.0)	1,4-Dioxane	80	13
6	Oxone (2.0)	DMF	80	42
7	BPO (2.0)	CH₃CN	80	10
8	K₂S₂O₈ (2.0)	CH₃CN	80	38
9	TBHP (2.0)	CH₃CN	80	0
10	(NH₄)₂S₂O₈ (2.0)	CH₃CN	80	Trace
11	Oxone (1.2)	CH₃CN	80	70
12	Oxone (1.2)	CH₃CN	r.t.	Trace

Entry	Oxidant (equiv.)	Solvent	Temp./℃	Yield^a/% of 3a
1	Oxone (2.0)	CH₃CN	80	61
2	Oxone (2.0)	DCE	80	20
3	Oxone (2.0)	THF	80	17
4	Oxone (2.0)	DMSO	80	44
5	Oxone (2.0)	1,4-Dioxane	80	13
6	Oxone (2.0)	DMF	80	42
7	BPO (2.0)	CH₃CN	80	10
8	K₂S₂O₈ (2.0)	CH₃CN	80	38
9	TBHP (2.0)	CH₃CN	80	0
10	(NH₄)₂S₂O₈ (2.0)	CH₃CN	80	Trace
11	Oxone (1.2)	CH₃CN	80	70
12	Oxone (1.2)	CH₃CN	r.t.	Trace

N-羟乙基-N-芳基丙炔酰胺的无金属硒化螺三环化反应

Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides

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